We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Old Naples Holiday Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Community
    Selected
    Payment
    Select
    Go to map view
    More filters
    loading...
    From
    $3,648
    / Night
    View Details
    1 / 30
    4.5 of 5 stars (8) Very good
    4 Bedrooms / 6 Bathrooms / Sleeps 8
    Overview Reviews (8) Make Enquiry
    From
    $1,642
    / Week
    View Details
    1 / 17
    5 of 5 stars (13) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (13) Make Enquiry
    From
    $4,468
    / Week
    View Details
    1 / 29
    5 of 5 stars (12) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (12) Make Enquiry
    From
    $958
    / Week
    Payment Protection
    View Details
    1 / 38
    4.5 of 5 stars (10) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Reviews (10) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Upon entering our spacious condominium nestled in the quiet golf community of Naples, Florida, the view of the lush vegetation, the golf course, and the placid lake sooths you. Sliding glass doors line the adjacent living room, dining room and kitchen, of this 3 bedroom 2 bath unit of more than... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 29 March 2015
    Some friends and I stayed at this condo last summer and like it so much, we are staying again next month. We loved the open concept of the condo, the close proximity to the pool...
    5 of 5 stars Reviewed 12 July 2013
    Had a great time, do not usually write reviews but have to respond. Some places do not suit everyone but this place was great and I'm picky. I'd come back again. Loved the...
    See all reviews
    From
    $3,511
    / Month
    View Details
    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Golfers and nature-lovers rejoice! Immerse yourself in Marengo, a stunning home away from home with a divine golf course view and superb lifestyle and beauty that only Florida has to offer. Fiddler’s Creek of South Naples encompasses nearly 4,000 acres, yet less than one-third of the land at... View all property information
    Make Enquiry
    From
    $3,798
    / Week
    View Details
    1 / 35
    5 of 5 stars (6) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    'Chatterbox Cottage' in the Heart of Olde Naples - Fantastic Location! Can walk to everything!!! Sophisticated unique luxurious four bedroom, two bath Cottage with heated swimming pool in the Historic District of Olde Naples on quiet street just a short 2 block walk to prestigious Fifth Avenue... View all property information
    Make Enquiry
    From
    $2,809
    / Week
    View Details
    1 / 22
    5 of 5 stars (7) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Location, location, location!!! This professionally managed 3 bedroom, 3 bath property in a spacious, lush and private garden is nestled in the heart of Olde Naples. The property is on a quiet street, lined with beautiful trees and just 3.5 blocks to Naples' pristine, white, sandy beaches as well... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 3 April 2014
    We just completed our second two month stay at Casa Piña and were set for next year, but unexpectedly bought a place of our own in Naples. This is a wonderful bright and...
    5 of 5 stars Reviewed 3 February 2012
    We were pleasantly surprised by this rental. The house is clean and functional and the pool was really nice for our teenagers. Everything worked well and the kitchen was well...
    See all reviews
    From
    $109
    / Night
    Payment Protection
    View Details
    1 / 9
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Walking distance to the beach and 5th Avenue in Olde Naples, Florida. Located in residential area of multi-million dollar homes. Only 14 units, super quiet. Plenty of parking, but you don't even need a car, walk to everything. All units overlook courtyard where pool & spa is located. View all property information
    Make Enquiry
    5 of 5 stars Reviewed 16 December 2014
    Our second time here at the White Sands Resort. Excellent location - minutes from the beach and shopping district. The condo was clean and ready to go when we checked in. Ed the...
    5 of 5 stars Reviewed 2 December 2013
    Just beautiful, comfortable, clean and very familiar .... Apartments super comfortable, the staff at the "top"! 5nta Avenida one minute walking. Very quiet with a gorgeous pool...
    See all reviews
    From
    $583
    / Night
    View Details
    1 / 31
    5 of 5 stars (8) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 9
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This casually elegant 3700 sq. ft. 4 bedroom home is located in the upscale neighborhood of Olde Naples. Located just steps away from one of Naples most pristine beaches and the Naples Pier. Charmingly designed, this home boasts 25 foot ceilings and lavish windows which provide for an open and... View all property information
    Make Enquiry
    4 of 5 stars Reviewed 21 May 2014
    Our family spent 4 days in this house while attending a wedding. We have been to Naples many times, but had never rented a house. It was perfect for our group. The location...
    5 of 5 stars Reviewed 13 January 2014
    We had a great time at the beach house. The huge master bedroom and and even larger master bath along with the three upstairs bedrooms (each with its own bath) admirably served...
    See all reviews
    From
    $1,021
    / Night
    View Details
    1 / 50
    5 of 5 stars (6) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Naples' best vacation home! Luxury Old Florida Beach House style pool home in heart of Old Naples prestigious Moorings. Lushly landscaped tropical pool area. Features one of the few private beaches in Naples. This home has been beautifully furnished by one of the countries top designers. No detail... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 10 August 2014
    Eight adults and four children had more than enough room in the Mermaid Cottage. We all fit around the table for meals and visiting. With two spacious living rooms the children...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $183
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (6) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    We have a lovely 2 bedroom plus den home on the 10th fairway of a private golf club with a stream running between the yard and the fairway which protects your privacy. The home is located on a cul-de-sac so it's a very quiet neighborhood. We are mid-way between Marco Island and Olde Naples and... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 30 June 2014
    What a great location and house. It was well appointed and the pool was very nice. They pond in back was great and I could feed bread to these huge turtles and fish. Had a great...
    5 of 5 stars Reviewed 11 June 2012
    we stayed in May and the house was perfect. A lovely location in a great spot close to centre of old naples. The house itself is very well equipped with everything you could...
    See all reviews
    From
    $351
    / Night
    View Details
    1 / 18
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    BRIARWOOD villa, yet another beautiful, well kept home in the heart of Naples offers both superb accommodation, great south facing views, privacy, security and close proximity to heart of Old Naples. This spacious 4 bed 3 bath home is within the community of Briarwood , an extremely popular gated... View all property information
    Make Enquiry
    From
    $300
    / Night
    View Details
    1 / 9
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautiful two-story 4 bedroom 3.5 bath home just one mile from the beach at Vanderbilt Beach. Close to Delnor Wiggins Beach Park and a parking pass to the beach park is provided. Excellent location for shopping and restaurants. Trader Joe's less than a mile. Whole Foods about 1.5 mi. A great... View all property information
    Make Enquiry
    Enquire for rates
    1 / 17
    5 of 5 stars (1) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Never miss a sunset from this beautifully appointed beach house just steps from Naples Famous fishing pier and beautiful white sand beaches. 4 bedroom plus den and game room, 4 1/2 Baths. Pool, Hot tub, summer kitchen, Jetted tubs in bathrooms, game room, 2 wet bars, widows walk, gourmet kitchen…... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 8 August 2014
    We stayed at the Naples Beach House for a week in June and it was wonderful. The house is furnished very comfortably for a family. The location is the best--less than a block to...
    See all reviews